What I Wish I Knew When I Was 20

Summary Written by Nicole Sheldrake
"Knowing that you can question the rules is terrifically empowering. It is a reminder that the traditional path is only one option available to you. You can always follow a recipe, drive on the major thoroughfares, and walk in the footsteps of those before you. But there are boundless additional options to explore if you are willing to identify and challenge assumptions, and break free of the expectations that you and others project onto you."

- What I Wish I Knew When I Was 20, page 53

The Big Idea

The World Through Different Lenses

"We can challenge ourselves every single day. That is, we can choose to view the world through different lenses – lenses that allow us to see problems in a new light. The more we take on problems, the more confident and proficient we become at solving them. And the better we are able to see them as opportunities."- What I Wish I Knew When I was 20, page 16

Most of us realize there are different ways of seeing the world – we all know people from different cultures or see the impact on our world of how other people think. However, most humans are very habitual in their thinking and actions. So much so that we find it extraordinarily difficult to gain a new perspective on anything. What I Wish I Knew When I Was 20 outlines specific tools and thinking skills that anyone can use to see their life in a new way and make changes for the better.

Insight #1

Inspiration through "recombining"

"Lucky people don't just pay attention to the world around them and meet interesting individuals – they also find unusual ways to use and recombine their knowledge and experiences."- What I Wish I Knew When I was 20, page 126

Next time you have to generate solutions to a problem, use this exercise from the book (p19) to see the problem from a new perspective and brainstorm more solutions.

Ask a friend to name a random object, the first thing that comes to their mind (don’t tell your friend what the problem is). Use that object to solve your problem. Come up with at least 10 solutions and write them all down. This gives you a chance to get into the flow of generating ideas and writing them down ensures you don’t forget any.

The random object takes you out of your habitual frame of reference for solving that problem, forcing you to find other resources and points of view.

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Insight #2

Question the rules

"[This book] is designed to give you permission to question conventional wisdom and to revisit the rules around you. There will always be uncertainty at each turn, but armed with the confidence that comes from seeing how others have coped with similar ambiguities, the stress will morph into excitement, and the challenges you face will become opportunities."- What I Wish I Knew When I was 20, page 14

Many of the choices we make are based on assumptions we have about life. Successful entrepreneurs question their assumptions as well as the conventional wisdom to seize opportunities. “Guy Laliberté started Cirque du Soleil by challenging every assumption about what a circus could be and in doing so transformed a problem – a dying industry – into an opportunity.” (p25)

The following exercise from the book (p25) makes it easy for anyone to question their assumptions then use those assumptions to look at their problems from a new perspective.

Make a list of all the assumptions you have about a particular problem – every aspect. Then turn these assumptions upside down by imagining the opposite of each one. Next, from both the original and upside-down assumptions, choose which ones you’d like to keep. What changes can you create to make those upside-down assumptions a reality? Some of them may be more realistic than you think.

What I Wish I Knew When I Was 20 literally changed my life – I started running a workshop based on the exercises and principles in the book. I even called the author and chatted to her on the phone after running my first workshop. She was as encouraging and high-energy as her book!

Read the book

Get What I Wish I Knew When I Was 20 on Amazon.

Tina Seelig

Tina Seelig is the Executive Director for the Stanford Technology Ventures Program (STVP), the entrepreneurship center at Stanford University’s School of Engineering. STVP is dedicated to accelerating high-technology entrepreneurship education and creating scholarly research on technology-based firms. STVP provides students from all majors with the entrepreneurial skills needed to use innovations to solve major world problems.

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